When Dean Met Cas
by RosesandThorns666
Summary: AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R! Rated M for language and content.
1. Chapter 1

**Summary: **AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I don't own anything concerning _When Harry Met Sally_, including some of the lines in this story.

**A/N: **Okay, I couldn't resist doing the Dean/Cas version of my favourite movie ever! Yes, Dean is bi in this so there are female and male partners, whereas with Castiel it's just male partners. I hope that you like this version, which I've dubbed _When Harry Met Sally: The Gay, _Supernatural _Version_.

Happy reading!

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><p><strong>When Dean Met Cas<strong>

**Chapter One**

_**1998**_

Twenty-six year old Dean Winchester holds twenty-one year old Lisa Braeden in his embrace, the two of them kissing tenderly as they say their long goodbye. Dean, the handsome dark blonde-light brunette with stunning green eyes has just completed law school and is about to head to New York, therefore leaving Lisa behind. Lisa is his dark brunette girlfriend who he's been with for a while now, and who he really does love and respect. They're at the University of Chicago, Lisa's good friend Castiel, who is also going to New York, is going to drive Dean there. Upon breaking their kiss, the two smile at each other, Lisa looking dreamily into Dean's eyes.

"I love you." She says softly, earning a smile from her boyfriend.

"I love you too." Dean replies, pressing a deep kiss to her lips and holding her close to him, not noticing Castiel pull up in his dark blue Ford Granada.

Castiel, the twenty-one year old with the unbelievably gorgeous blue eyes and near-black hair, sits patiently and waits for the two to finish kissing. He watches them, beginning to feel uncomfortable as Lisa's backside gets fondled by the insanely hot guy she's kissing. Eventually he clears his throat, breaking them out of their kiss. He's heard about the fact that Dean's bisexual, so doesn't worry about any prejudice about him being gay.

"Oh, hey there, Cas!" Lisa says sweetly, Dean looking around to find a guy sitting in the driver's seat.

_Cas is a guy? _

"Cas, this is Dean Winchester," Lisa begins, "Dean, this is Castiel Novak."

"Nice to meet you." Dean says with a soft smile, watching Castiel smile up at him.

"You want to drive the first shift?" He asks, Dean shaking his head softly.

"No, you're already there, you can start." He replies, Castiel letting him know that the back's open for him to put his things in.

Dean packs his bags, and while he promises Lisa to call him and they start to kiss again. This is disgusting. He doesn't want to sit and bear witness to this, he wants to start the drive to New York. He beeps the horn, breaking the two apart while smiling sweetly at them. Ah, he loves Lisa very much, but watching Dean and her eat each other's faces off? No, thank you!

"Sorry!"

As Dean and Lisa say their final goodbyes, Dean climbs into the car beside Castiel and the two head away from the university and set off to New York. The drive is quiet to begin with, so Castiel decides to explain how he's planned the journey.

"Okay, I've figured all this out," He began, "We can do six shifts of three hours each or I've broken it down by mileage..."

He's cut off when Dean's gorgeous ass comes right into his view as the older man leans into the back to get something from his bag. God, it is a nice ass. Castiel has to keep his eye on the road, but it's so difficult when that beautiful backside is in his view.

"Th-there's a map on the visor which I've marked to show the locations where we can change shifts." He says, getting a shock when Dean sits back with a handful of grapes and shoves them in Castiel's face.

"You want a grape?"

Castiel turns back to focus on the road and shakes his head lightly.

"I don't like to eat between meals."

Dean spits out the grape seeds and Castiel sighs, reserving his anger as Dean turns back to him with a blank face.

"I'll roll down the window." He says, "So, why don't you tell me the story of your life?"

Another set of seeds are spat out of the window and Castiel shudders at the utter foulness of it, continuing to drive and finding a way to tell Dean that nothing much has happened in his life yet.

"The story of my life?" He asks, Dean nodding and munching on another grape.

"We've got eighteen hours to kill before we get to New York, so..." He says, spitting out more seeds.

"The story of my life won't even get out of this city, Dean." Castiel replies, "I mean, nothing's happened to me yet...Apart from finding out I was gay at the age of fifteen. That's why I'm going to New York."

"So something will happen to you?" Dean asks, Castiel nodding softly, "Like what?"

"Well, for a start I'm going to journalism school to become a reporter." He replies, waiting for Dean's answer.

He knows he won't like it because so far, Dean seems to be a bit of an ass. How right he is.

"So you can write about things that happen to other people?"

Castiel waited for a moment before speaking, since Dean's made him feel kinda bad about it.

"That's one way to look at it." He says quietly, barely able to bear Dean's next unbelievably dampening words to him.

"Suppose nothing happens to you." The older man says, "Suppose you live your whole life, nothing happens to you, you never meet anyone, you never become anything and you die one of those New York deaths that no-one knows about until two weeks later when the smell drifts into the hallway."

Castiel looks across at Dean who continues to eat his grapes, unaware that the young man next to him is actually terrified of spending the next eighteen hours in complete torture with this man who just astounds him with the things he comes out with.

When they reach the highway, the two have spoken some more and know each other a little more, so Castiel turns onto the topic of Lisa.

"Lisa said you had a dark side."

"Yeah," Dean says with a lopsided grin, "That's what drew her to me."

"Your dark side?" Castiel asks, earning a nod from Dean.

"Yeah, don't you have a dark side?" He asks, "No, you're probably one of those cheerful people who dots their 'i's with little hearts."

Castiel feels like he needs to defend himself now, because Dean is just blatantly ripping him to shreds and it hurts a little bit.

"I have just as much of a dark side as the next person."

"You do?" Dean asks, "Y'know when I get a new book, I read the last page first. That way, if I die before I get to the end, I know how it turns out. That, my friend, is a dark side."

"That doesn't make you deep or anything," Castiel begins, realising that he is in fact, a happy person, "Alright, basically I'm a happy person, and I don't see where the problem is with that."

"Of course you don't, you're too busy being happy." Dean says, "Do you ever think about death?"

Castiel pauses for a moment. He does think about death, just not as often as Dean probably does. It seems that Dean is one of those people who seems to have one up on every one else. Your typical ass. Perfect!

"Yes."

"Sure you do. A fleeting thought that drifts in and out of the transom of your mind." Dean says, "I spend hours. I spend days..."

"And this makes you think you're a better person?" Castiel snaps, finally pissed off with Dean and his attitude.

"Look, when Death finally comes for me, I'm gonna be prepared and you're not." Dean tells his him, calm to a point where Castiel could rip the steering wheel of his car out and beat him to death with it, "That's all I'm saying."

"Yeah?" Castiel asks, "And you're gonna ruin you're whole life waiting for it."

Dean's silence makes Castiel believe one thing. He's finally gotten to him.

That on its own brings a small smile to his lips.

-TBC-

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><p><strong>Hope you enjoyed!<strong>

**Thanks for reading so far!**

**xxxxxxxxxxxxxx  
><strong>


	2. Chapter 2

**Summary: **AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I don't own anything concerning _When Harry Met Sally_, including some of the lines in this story.

**A/N: **The "Men and women can never be friends" thing doesn't apply in this story! But, I hope you like it all the same. Here's chapter two and thanks for the support with chapter one!

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><p><strong>When Dean Met Cas<strong>

**Chapter Two**

"He doesn't want her to stay, that's why he puts her on the plane." Dean says as they continue to drive.

It is now night time, and Dean's taken over his shift of the drive, and the two are arguing about the movie _Casablanca_. Castiel seems to really go for the woman's side of things, and Dean doesn't think he's feminine at all, but it appears he really understands the female perspective of things.

"I don't think she wants to stay!" Castiel argues, Dean shaking his head at the opinion.

"Of course she wants to stay!" He says, "Wouldn't you rather be with Humphrey Bogart than the other guy?"

"I don't want to spend the rest of my life in Casablanca married to a man who runs a bar!" Castiel replies, "That probably sounds incredibly snobbish to you, but I don't."

"You'd rather have a passionless marriage..."

"...And be the first Lady...or second Lord of Czechoslovakia..."

"...Than live with the man you've had the best sex of your life with, just because he owns a bar and that's all he does."

Dean pulls up outside a diner, watching as Castiel runs his hands through his hair and spikes it up a little bit, as if it needs doing any more. He has to say that the hair on this guy is incredible. It's like unbelievably amazing sex hair and he actually finds it incredibly attractive, but decides to focus more on the meal that's heading his way.

"Yes, and so would any woman in her right mind," Castiel begins, "Women are very practical; even Ingrid Bergman, which is why she gets on the plane at the end of the movie."

The two get out of the car and Dean nods as though confirming a suspicion which alerts Castiel because he knows he's going to get some kind of put-down from Dean again.

"I understand." Dean says, walking towards the diner which concerns Dean a little.

"What?" Castiel asks, Dean shaking his head.

"Nothing?"

"What?"

"It doesn't matter?"

Castiel feels angry now and finally snaps, grabbing Dean's arm to spin him around so they're facing each other.

"No, just tell me!"

"Clearly, you haven't had great sex yet."

Castiel feels so offended that he could just drop down on the spot and he's in the right mind to just abandon Dean here and carry on to New York on his own, but he's made the promise to Lisa and he won't break that promise because he loves her dearly.

"Two, please..." Dean says as they enter the diner, the hostess leading them to their seats.

"Yes, I have." Castiel protests, Dean just shaking his head.

"No, you haven't."

"It just so happens that I have had _plenty _of good sex." Castiel says, a little too loudly as the whole restaurant stops and stares at him.

Perfect. In his embarrassment, he just wanders over to the table and sits opposite Dean who's already trawling through the menu. This night is way too long already, and he has many more hours of Dean's annoying mannerisms. He's just so rude and so...angsty a lot of the time. The things he says just wind him around the bend quicker than he can drive the car. And the way he drives scares Castiel a little.

"With whom?" Dean asks, confusing Castiel slightly.

"What?" He counters, Dean continuing to scout over the menu, putting it down to face him.

"With whom did you have this great sex?" He asks, Castiel gazing at him with an expression of both offence and confusion.

"I'm not gonna tell you that!" The younger man says, completely embarrassed by Dean's question.

"Fine. Don't tell me." Dean says, looking back to the menu while Castiel fidgets with his, still shocked, confused and offended all at once.

He goes to look at the menu but suddenly decides to tell Dean who he head sex with, which confuses him greatly again because why would he tell a stranger? But he does.

"Raph Adler."

"Raph? Raphael?" Dean asks, "No, you did not have great sex with Raphael."

"I did too!" Castiel contradicts, the feeling in his gut telling him that Dean is going to go on a little rant again.

"No, you didn't." He says, "A Raphael can do your income taxes. If you need a root canal, Raphael's your man, but humpin' and pumpin' is not Raphael's strong suit. It's in the name."

Castiel looks even more horrified as Dean continues, and then things just go out of proportion.

"_Do it to me, Raphael. You're an animal, Raphael. Ride me hard, _Raphael." He says, shocking Castiel further, "It doesn't work."

Thankfully, a waitress approaches the table, and Castiel breathes a sigh of relief he doesn't know he's been holding in and Dean orders straight away.

"I'll have the number three."

The waitress turns to Castiel and smiles, not knowing what kind of horror was waiting for her with this order.

"I'd like the chef salad, please, with the apple pie a la mode." Castiel begins as the waitress takes his order, "But, I'd like the pie heated, and I don't want the ice cream on top, I want it on the side. And I'd prefer strawberry instead of vanilla if you have it. If not, then no ice cream, just whipped cream, but only if it's real. If it's from a can, then nothing."

"Not even the pie?" The waitress asks.

"No, just the pie, but then not heated."

The waitress leaves, while Dean just stares at Castiel in disbelief. He's never experienced any kind of ordering like that before, and quite frankly it made him a little nervous to see how high maintenance Castiel really is.

"What?" Castiel asks when he notices the way Dean's looking at him, like he has two heads or something.

"Nothing." Dean says, the two returning to slightly awkward silence, "So how come you broke up with Raphael?"

"How do you know we broke up?" Castiel asks, feeling his stomach rumble at the thought of the apple pie he's ordered.

"Because if you hadn't, you would be here with me." Dean says, "Okay? You'd be off with Raphael the Wonder Schlong."

Castiel looks a little mortified, and Dean knows he has this effect on him and it makes him chuckle inwardly.

"First off, I am not _with _you." Castiel says with a warning look, "And second, it's absolutely none of your business whatsoever why we broke up."

"You're right. You're right." Dean replies, "I don't wanna know."

There's a pause, and Castiel knows that he's going to tell him again, despite the fact that he doesn't want to at all, but he can't stop himself.

"If you must know," He begins, "It was because he was very jealous, and I had these days of the week boxer shorts."

Dean made a buzzing sound and sat forward a little.

"I'm sorry, I need judge's ruling on this." He says, "Days of the week boxer shorts?"

"Yes. They had the days of the week on them, and I thought they were sort of funny." Castiel explains, "But then, one day he said to me, _'You never wear Sunday'. _It was all suspicious. Where was Sunday? Where had I left Sunday? And I told him, and he didn't believe me!"

"What?" Dean asks.

"They don't make Sunday." Castiel tells him, leaving Dean looking a little confused and shocked.

It's nice to return the feelings. Especially since Castiel has spent most of this evening feeling like this.

"Why not?" Dean asks.

"Because of God." Castiel replies, leaving Dean looking astounded.

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><p>"So fifty percent of my share is...six-fifty..." Castiel mutters as he works out the half of the bill, finding Dean staring at him in a way which makes him feel a little nervous.<p>

"What?" He asks, "Is there something on my face?"

"You're a very attractive person." Dean says quietly, Castiel gazing at him with slight shock and confusion.

He then remembers that Dean is bisexual, and also remembers that he's dating Lisa. Castiel is Lisa's best friend, and if Dean carries on with what Castiel thinks he's doing, he doesn't know what he'll do.

"Oh..." He says, "Thank you."

"Lisa never said you were so attractive..." Dean replies, Castiel blinking at him slightly.

"I'm not surprised, since you're her boyfriend and I'm a guy..." He says, "Maybe she doesn't think I'm attractive."

"It's not a matter of opinion." Dean tells him, "Empirically, you are attractive."

The two leave their money on the table and go to leave, Castiel looking at Dean with shock.

"Lisa is my friend."

"So?" Dean asks.

"So, you're going with her!" Castiel exclaims in a hushed voice.

"So?" Dean asks again.

"So, you're coming onto me!" Castiel cries again, Dean immediately defending himself.

"No, I wasn't!" He replies, Castiel looking completely offended and heading to the car to begin the next shift of driving, "What? Can't a person tell someone they're attractive without it being a come-on? Alright, let's just say for the sake of argument it was a come-on. Okay? What do you want me to do? I take it back, alright? I take it back."

Castiel stares at him from the driver's side and shakes his head slightly.

"You can't take it back." He says.

"Why not?"

"Because it's already out there."

There's an awkward pause and Dean suddenly cries out, making Castiel jump.

"Oh, jeez! What are we supposed to do? Call the cops, it's already out there!"

"Just let it lie, okay?" Castiel says, climbing into the car as Dean does and rolling his eyes as Dean begins to speak again.

"Right, right...Let it lie." He says, "That's my policy. Let it lie."

There's another pause.

"You wanna spend the night in a motel?" He asks, "You see what I did? I didn't let it lie."

"Dean..."

"I said I would and then I didn't..."

"Dean..."

"I went the other way."

"Dean!" Castiel says, finally having enough, "We're just going to carry on with this trip, okay?"

"Fine. Best thing." Dean replies, the two setting off for the next leg in their journey.

-TBC-

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><p><strong>Hope you enjoyed!<strong>

**Thanks for reading so far!**

**xxxxxxxxxxxxxx  
><strong>


	3. Chapter 3

**Summary: **AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I don't own anything concerning _When Harry Met Sally_, including some of the lines in this story.

**A/N: **Thanks for the support so far! I'm so glad you're enjoying this! Hope you like this chapter!

xxxxxxxxxxxxx

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><p><strong>When Dean Met Cas<strong>

**Chapter Three**

Finally Dean and Castiel arrive in New York. It's a beautiful day and as Castiel pulls up, he realises that Dean's the only person he knows in New York. It's a shame that they aren't going to be friends. The two get out of the car and Dean stretches, heading around to the trunk to get his things.

"Well, it was nice knowing you." He says as he gets ready to leave, watching the weak smile that crosses Castiel's face.

"Yeah. It was interesting." The younger man replies, Dean smiling in response.

"Yeah. Thanks for the ride." He says, Castiel smiling in return.

"You're welcome."

Awkward silence falls over the pair again as they nod at each other before Castiel holds out his hand for Dean to shake, which the older man does before grabbing his bags.

"Have a nice life." Castiel calls, Dean turning and grinning at him.

"You too."

And Castiel watches Dean Winchester walk out of his life, before he gets into the car and drives away to his own apartment. He reflects on the last eighteen hours and decides to never get involved with a man as obnoxious as him.

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><p><em><strong>2003<strong>_

Castiel allows Nick's lips to stay against his own as they kiss tenderly to say their goodbye. The two hold each other close, forgetting the hustle and bustle of the airport around them as Castiel prepares himself to leave Nick for this business trip. He really doesn't want to go, but at least Nick has come with him to say goodbye.

As they kiss, they don't notice someone staring at them until Castiel breaks the kiss and nudges Nick gently a little frightened. The man looks strangely familiar but Castiel really can't place him as hard as he tries.

"Nick, I thought it was you," The man says, "I thought it was you! Dean Winchester."

He holds out his hand and Nick shakes it, happy to see Dean while Castiel suddenly remembers who it is and really, really hopes that Dean can't place him.

"Dean, how are you?" Nick asks.

"I'm good, thanks." Dean replies, "What about you?"

"Fine, fine." Nick says with a grin, incredibly happy to see the man who Castiel couldn't stand in the slightest.

"Still with the D.A's office?" Dean asks, Nick shaking his head.

"No, I switched to the other side." He laughs, "How about you?"

"I work with a small firm," Dean replies, "We do political consulting."

They nod and there's an awkward silence, which Castiel notices happen so often around Dean.

"Oh, Dean, this is Castiel Novak," Nick says softly, "Cas, this is Dean Winchester. We used to live in the same building."

Dean knows he's seen this guy somewhere. The hair and eyes are so familiar it's unbelievable but he just can't place him. The name seems really rare too, surely he'd remember a guy called Cas...

"Hi..." He says with a smile, Castiel just nodding in response, "Well, it's been great to see you. I'll see you around."

"Bye." Nick says softly, watching Dean as he makes his way down the corridor a little confused.

"Thank God he couldn't place me." Castiel says with a slightly disgusted look on his face, "I drove from college to New York with him five years ago and it was the longest damn night of my entire life."

"What happened?" Nick asks, listening intently as his beautiful blue-eyed angel turns around to speak to him.

"He made a pass at me and when he said no – He was going with a girl friend of mine...Oh, God, I can't remember her name!" Castiel says, slightly mortified with himself, "Don't get involved with me, Nick, I'm twenty-six years old and I can't even remember the name of the girl I was such good friends with that I wouldn't get involved with her boyfriend."

Nick knows about Dean being bisexual, and it doesn't come as a great surprise that he tried it on with Castiel.

"So, what happened?" Nick asks.

"When?" Castiel counters, slightly confused.

"When he made a pass at you and you said no?"

"Oh...Um..." Castiel replies, "Nothing, strangely. We just carried on with the drive."

Nick nods and leans in for another kiss, Castiel suddenly sighing with relief.

"Lisa Braeden!" He cries, "That was her name! Thank God!"

"I'll miss you." Nick says, drawing Castiel's attention to him, "I love you."

Castiel's face breaks into a breathtaking smile.

"You do?" He asks, earning a nod and a grin from Nick, "_I _love _you_."

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><p>Castiel's dreamy smile hasn't left his face since that confession of love, and even though he is sat in between two complete strangers on his flight to Washington, he can't help but think of Nick's full lips around his own, and those words playing over in his head.<p>

_I love you_.

Behind the seats, Dean is watching Castiel curiously, because he knows he's seen the guy somewhere! He's trying so hard to remember but sits back in his seat when the stewardess approaches with the drink cart, asking the passengers what they'd like to drink. When she arrives at Castiel, he smiles softly at her.

"Do you have any Bloody Mary mix?" He asks, earning a nod from the stewardess, "No, wait. Here's what I want. Regular tomato juice filled up about three quarters, and then add just a splash of the Bloody Mary mix; just a splash, then with a piece of lime on the side."

"The University of Chicago, right?" Dean asks, Castiel turning around and sighing.

"Yes."

The man beside them looks curious at the two, while Castiel turns and decides to explain before Dean does.

"We drove from Chicago to New York together after graduation."

"Would you two like to sit together?" The man offers, Dean agreeing and thanking him before Castiel can even protest.

As Dean settles in his seat, Castiel knows that this plane ride is just going to be terrible.

"You were a friend of...oh, jeez..." Dean begins, Castiel sighing.

"Lisa's." He says, "I can't believe you can't remember her name."

"Sure, I do." Dean replies, "It was Lisa Raegan."

"Braeden." Castiel corrects with annoyance.

"Braeden, right. That's what I said," Dean says, "Whatever happened to her?"

"I have no idea." Castiel replies, taking in Dean's shocked face.

"You have no idea? You were a good friend of hers!" Dean says, "We actually didn't make it because you were such good friends."

"You went with her." Castiel says, looking a little pissed.

"And was it worth it?" Dean asks, "The sacrifice for a friend you don't even keep in touch with."

"Dean, I swear to you that I never considered not sleeping with you a sacrifice." Castiel replies, barely able to believe Dean's arrogance.

"Fair enough." Dean says, "Fair enough. You were going to be a gymnast."

"A journalist." Castiel corrects him again.

"That's what I said." Dean says, "Did you?"

"I'm a journalist. I work at the News." Castiel replies, reading the paper on his lap and trying to ignore him.

"Great, and you're with Nick." Dean says, "You've been together for what, three weeks?"

"A month." Castiel replies, "How did you know that?"

"You take someone to the airport, it's clearly the beginning of a relationship," Dean explains, "Which is why I've never taken someone to the airport at the beginning of a relationship."

"Why?" Castiel asks.

"Because, eventually, things move on and you don't take someone to the airport, and I've never wanted to have anyone say to me, 'How come you never take me to the airport anymore?'."

"It's amazing." Castiel says, wishing he'd never bothered to ask why, "You look like a normal person, when actually, you're just the angel of death."

"Are you gonna marry him? Or get a civil partnership?" Dean asks, Castiel sighing quietly.

"We've only known each other for a month," He explains, "Besides neither one of us is looking to get married or get a civil partnership right now."

"I'm getting married." Dean says, astounding Castiel completely.

"You are?"

"Yep." Dean replies.

"_You _are?" Castiel asks, earning a nod, "Who is she...? Or he?"

"Anna Milton," Dean answers, "She's a lawyer, she's keeping her name."

Castiel can't believe what he's hearing. Dean Winchester getting _married_. Clearly, he's more straight than gay, but that doesn't matter. He's getting married? Actually married to someone who will willingly marry him? He lets out a chuckle and Dean looks a little offended.

"What's so funny about that?"

"Nothing, nothing." Castiel replies, "It's just so optimistic of you, Dean."

"You'd be amazed at what falling madly in love can do for you." Dean replies with a smile, Castiel smiling in response.

"Well, that's wonderful." He says, "It's so nice to see you embracing life in this manner."

"Besides, you just get to a certain point in life when you just get tired of the whole thing." Dean says.

"What whole thing?" Castiel asks, wishing he hadn't.

"The whole life-of-a-single-guy thing." Dean replies, "Y'know when you meet someone, you have the safe lunch, where you decide you like each other enough to go onto dinner. You have dinner, do the white man's overbite..."

He even does a little motion which disgusts Castiel greatly.

"Then you go back to his or her place, you have sex, and you know what goes through your mind?" He asks, "How long do I have to lie here and hold them before I can get up and go home? Is thirty seconds enough?"

Castiel feels sick at those words and gazes at Dean with shock and almost horror plastered onto his face.

"That's what you're thinking?" He asks, "Is that true?"

"Sure, all men think that." Dean replies, "How long do you like to be held after? All night, right? You see that's your problem. Right there, between thirty seconds and all night is your problem."

"I don't have a problem." Castiel replies, offended, even more so at Dean's reply.

"Yeah, you do."

The rest of the flight is silent and after it Castiel really hopes he doesn't have to see Dean ever again.

-TBC-

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><p><strong>Hope you enjoyed!<strong>

**Thanks for reading so far! **

**xxxxxxxxxxxxxx  
><strong>


	4. Chapter 4

**Summary: **AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I don't own anything concerning _When Harry Met Sally_, including some of the lines in this story.

**A/N: **Thanks for all the support so far! We stay in the 2008 period and move through the next couple of years with Dean and Castiel. Hope you enjoy!

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><p><strong>When Dean Met Cas<strong>

**Chapter Four**

_**2008**_

"So, I looked through his pockets, okay?"

Castiel sighs as his best friend Gabrielle Singer talks about her love affair with a married man. She somehow manages to find married men and sleeps with them, but she also likes bisexual men, since she's that way inclined herself and Castiel has never understood why this is her way of thinking and living. It just is. She brushes a hand through her fluffy light brown locks and waits for the usual responses from her friends. She has the most beautiful hazel eyes, Castiel thinks, and he can't understand how she isn't settled down.

"Gabby, why were you looking through his pockets?"

This is his other friend, Jo Harvelle. Jo's married to a man named Crowley Masters, who happens to love the bones of her and treats her like a princess. Castiel is a little jealous of this but doesn't really like to think he is. He watches Gabrielle and realises that perhaps she wants a taste of what Jo has. The good thing about the female friends is that Castiel really gets the woman's perspective on things. He really, really thinks that women have it bad in life with the fact that they suffer monthly with periods, men think they can treat them like they're inferior, and they have to go through childbirth. Really, he does honest to God feel sorry for them.

"And you know what I found?" Gabrielle asks.

"What?" Jo counters.

"They just bought a dining room table." Gabrielle says with a hint of annoyance, "He and his wife just went out and spent sixteen hundred dollars on a dining room table."

"Where?" Jo asks with shock.

As good as the money she and her husband earn is, they can't ever and wouldn't ever spend sixteen hundred dollars on a stupid dining room table. Eight hundred is enough as it is for a whole set!

"The point isn't where, Jo!" Gabrielle says with slight exasperation, "The point is he's never gonna leave her!"

"What else is new?" Jo asks, "You've known this for two years."

"You're right." Gabrielle replies, "You're right, I know you're right."

"Why can't you find someone single?" Jo asks, "When I was single I knew lots of nice single men. There must be someone! Cas found someone."

"Cas got the last good one." Gabrielle says glumly, Castiel finding this the perfect time to bring this up.

"Nick and I broke up."

"What?" Jo asks with shock.

"When?" Gabrielle asks, also completely shocked.

Nick and Castiel were a real couple, a dream couple almost. So, why had they broken up? Things have always seemed to be perfect between them. Obviously not.

"Monday." Castiel replies.

He actually feels really quite okay with it. He's had the opportunity to get used to coming home to an empty apartment, and he quite likes being on his own again. It's nice to have the time for himself that he needs that sometimes he couldn't have because of his commitments with Nick. Maybe it was for the best. They had been growing further and further apart for a while.

"You've waited three days to tell us?" Jo asks, barely able to believe what Gabrielle comes out with next.

"You mean Nick's available?"

"For God's sakes, Gabrielle! Don't you have any feelings about this?" Jo asks with annoyance, "He's obviously upset!"

Ah, Jo had always been so sensitive in her own way, bless her heart. She knows just how to look after everyone else, and she clearly wants to look after Castiel. He doesn't mind that. He likes her protectiveness.

"I'm not that upset," He protests, "We've been growing apart for quite a while."

"But you guys were a couple, you had someone to go places with." Gabrielle states, "You had a date on national holidays!"

"I just said to myself, 'You deserve more than this. You're thirty-one years old'..."

"And the clock is ticking." Gabrielle says.

"For you ladies, yes, but not for me." Castiel replies taking a sip of his wine, "Oh, and the clock doesn't really start to tick until you're thirty-six."

"God, you're in such great shape." Jo says with sympathy in her eyes.

"Well, I've had a few days to get used to it," Castiel says, smiling as he continues, "And...I feel okay."

"Good." Gabrielle replies, "Then you're ready."

Going into her satchel, Gabrielle finds a box full of cards with numbers on them, and while Castiel watches curiously, Jo is absolutely shocked and aghast at what she's seeing.

"Really, Gabby!" She scolds, Gabrielle shaking her head and opening it up, pulling out a card.

"How else do you think you do it?" She asks, "I've got the perfect guy. I don't happen to find him attractive but you might."

She looks to Jo.

"He doesn't have a problem with chins."

"Gabby, I'm not ready, honey." Castiel says, slightly annoyed.

"But you just said you were over him." Gabrielle protests.

"I _am _over him." Castiel tells her, "But I'm in a mourning period."

There's a small silence and he gives in. Damn Gabrielle and her way of sparking his curiosity. He can just sense that something is going to come up that he doesn't like. It has often been the case in his life, but he gives in regardless.

"Who is it?"

"Alistair Anderson." Gabrielle replies.

"Oh!" Jo cries in disbelief, breaking into soft laughter.

"You fixed me up with him six years ago!" Castiel replies, both he and Jo laughing a little at her.

"I'm sorry!" She says with a smile, pulling out another card, "Balthazar Adler."

"He's been married for over a year!" Castiel tells her, watching her face curiously.

"Really?" She says quietly, folding the corner of the card over, "Married..."

She places the card back and goes to pull another one out, Castiel finally deciding he's had enough.

"Look, there is no point in my going out with someone I might really like if I met him at the right time, but who right now has no chance of being anything to me but a transitional man."

"Alright, but don't wait too long." Gabrielle says softly, "You know what happened to Adam Milligan? His wife left him and everyone said, 'Give him some time, don't move in too fast.'...Six months later, he was dead."

Castiel just stares in disbelief.

* * *

><p>The Mexican wave comes around again and Dean Winchester and his best friend Sam Wesson get up and join in without any real emotion or spark. Dean's had a crappy time recently, and Sam's taken him to a football game to try and take his mind off things.<p>

"When did this happen?" Sam asks, concerned for his friend.

"Friday." Dean sighs, "Anna comes home, she says, 'I don't know if I wanna be married anymore.' Y'know, like it's the institution. Like, it's nothing personal, it's just something she's been thinking about in a casual way."

Sam listens intently, understanding that Dean needs him right now and he knows he'll do whatever he can.

"I'm calm, I say, 'Why don't we think about it? Take some time, don't rush into anything?'" Dean continues, "Next day, she says that she's thought about it and she wants a trial separation. She just wants to try it, she says, but we can still date, like this is supposed to cushion the blow."

Sam just listens as he continues, neither of them paying attention to the game.

"I mean, I got married so I could stop dating, so I don't see this as a big incentive since the last thing you wanna do is date your wife, who's supposed to love you." Dean explains, "Which is what I'm saying to her when it enters my mind that, perhaps, she doesn't. So I say to her, 'Don't you love me anymore?' and she says, 'I don't know if I've ever loved you.'"

The wave returns and comes through the crowd, Dean and Sam standing up to join in. Sam is freakishly tall, Dean realises, and he's six foot two. He has a giant as a friend. That's pretty cool, he thinks.

"Oooh, that's harsh!" Sam says as they take part in the wave and sit back down, "You don't bounce back from that right away."

"Thanks, Sam." Dean says, Sam patting his shoulder.

"No, dude, I'm a writer, I know dialogue," He says, "And that is particularly harsh."

"And the she says she just found out that someone at her office is going to South America and that she can sublet his apartment. I can't believe this..." Dean continues, "Then the doorbell rings. 'I can sublet his apartment'. The words are still hanging in the air, like in a little balloon attached to her mouth..."

"Like a cartoon." Sam says.

"Yeah, so I go to the door, and there are moving men there." Dean says, Sam unable to believe what he's hearing, "Now, I'm starting to get suspicious, and I ask her, 'Why did you call these movers?' and she says _nothing _to me at all, so I turn to the movers and ask, 'When did this woman book you for this gig?' And they're just standing there, three huge guys, one of 'em wearing a t-shirt that says 'Don't fuck with Mister Zero.'"

Dean looks so sad right now that Sam feels so sorry for him he could just hug him. But Dean isn't too fond of hugs, so they avoid it.

"So, I say, 'Anna, when did you make this arrangement?', and she says, 'A week ago.'" Dean continues, "And I say, 'You've known for a whole week and didn't tell me?' and she says, I can't believe this, by the way; she says, 'I didn't wanna ruin your birthday.'"

The wave comes around again and they both take part again before returning to their conversation.

"So you're saying Mister Zero knew you were getting a divorce a week before you did?" Sam asks.

"Mister Zero knew." Dean replies, leaving Sam even more horrified.

"I can't believe this!" He cries.

"I haven't told you the bad part yet." Dean sighs.

"What could be worse than Mister Zero knowing?" Sam asks, not really knowing what could possibly make this any worse.

"It's all a lie. She's with somebody else. Some tax attorney. She moved in with him." Dean says quietly.

"How did you find out?" Sam asks.

"I followed her, I stood outside the building." Dean replies.

"That's so humiliating." Sam tells him.

"Tell me about it." Dean says, "I knew. The whole time I knew that even though we were happy, it was just an illusion and one day, she'd kick the shit out of me."

"Marriages don't break up on account of infidelity." Sam explains, "It's just a symptom that something else is wrong."

"Oh, really?" Dean asks as another Mexican wave approaches, "Well, that symptom is fucking my wife."

-TBC-

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><p><strong>Hope you enjoyed! <strong>

**Thanks for reading so far! **

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><strong>


	5. Chapter 5

**Summary: **AU. Dean meets Castiel, and after a long drive to New York, they go to get on with their own lives. But what happens when fate keeps bringing them together? Please R&R!

**Disclaimer: **I don't own _Supernatural _or its characters. I don't own anything concerning _When Harry Met Sally_, including some of the lines in this story.

**A/N: **Thanks for all the support so far! I love writing this fic, since the movie is based on is my favourite! Hope you enjoy!

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><p><strong>When Dean Met Cas<strong>

**Chapter Five**

Gabrielle and Castiel are in the bookstore, both looking through books in the _Personal Relationships _section. Both feel the need to be looking at books in this area right now, and Gabrielle finds this the perfect time to bring up the topic of the married man she was having an affair with.

"So, I just happened to see his _America Express _bill." She says, catching Castiel's attention immediately.

He doesn't like to see Gabrielle in such a confused state with the guy she's seeing. She knows he's never going to leave his wife, yet she still sees him, and Castiel hates the man for treating her this way, but it's her life, and the choices she makes are hers and hers alone, and she must suffer any consequence of her decisions. He feels awful about letting her go through it though, but all he can say is that the man Gabrielle is seeing will never, ever leave his wife.

"What do you mean you just happened to see it?" He asks, moving a little closer to Gabrielle.

"Well, he was shaving," Gabrielle explains, "And there it was in his briefcase."

"What if he came out and saw you looking through his briefcase, Gabby?" Castiel questions.

"You're missing the point, honey, I'm telling you what I found." Gabrielle replies, "He just spent a hundred and twenty dollars on a new nightgown for his wife. I don't think he's ever gonna leave her."

"No-one thinks he's ever gonna leave her." Castiel says with a sympathetic frown, watching the spectrum of emotion flash across Gabrielle's beautiful eyes.

"You're right, you're right." She says, "I know you're right."

She looks up from a book at that moment, and sees an incredibly handsome man staring at Castiel, who's oblivious to the sex eyes he's getting. God, the guy is gorgeous, and Castiel is clearly the one he's staring at.

"Someone is staring at you in _Personal Growth_." She whispers to Castiel who looks up from the book he's looking at and feeling shock at the familiar pair of eyes gazing at him.

"I know him." He whispers quietly to Gabrielle, "You'd like him, he's married, and bisexual."

"Who is he?" She asks.

"Dean Winchester." He replies, "He's a political consultant."

"He's cute." Gabrielle says, shocking Castiel a little.

"You think he's cute?" He asks, knowing that he doesn't really agree with her.

"How do you know he's married?" She counters, both of them looking at Dean while he pretends to read his book.

"Because the last time I saw him," Castiel answers, "He was getting married."

"And when was that?" Gabrielle asks.

"Six years ago." Castiel replies.

"So, he might not be married anymore..." Gabrielle says with a soft smile.

"Also, he's obnoxious." Castiel tells her.

"This is just like in the movies, remember?" Gabrielle asks, "Like in _The Lady Vanishes_, where she tells him he's the most obnoxious man she's ever met."

"The most contemptible." Castiel corrects.

"And then, they fall madly in love." Gabrielle finishes.

"Also, he never remembers me." Castiel says, not knowing that Dean was almost right by his side.

"Castiel Novak."

He looks up and smiles his softest smile at the other man, deciding that being pleasant and civil is the best thing to do.

"Hi, Dean." He replies gently.

"I thought it was you." Dean says softly.

"It is." Castiel says with a sweet smile, "This is Gabrielle..."

He turns to see Gabrielle heading down the stairs to the lower floor of the bookstore and silently curses her for leaving him, but waves in return as she does. He realises that she think he and Dean should be alone for their reunion.

"Was Gabrielle." He says with a soft laugh, turning back to Dean and shrugging.

"How are you?" Dean asks, eyes soft and warm which Castiel has always remembered about him.

"Fine." He replies with a nod.

"How's Nick?"

Castiel's heart stops for a moment at that question, and he puts on a brave face. He has to. He can't get so upset about a guy. He's used to being single again now. He's okay with it, really. He has nothing at all to worry about, absolutely nothing. Positivity is the key, he knows this as a fact. He's over Nick. He's really, really over him.

"Fine." He replies, "I hear he's fine."

"You're not with Nick anymore?" Dean asks, looking a little shocked.

"We just broke up." Castiel replies, half expecting a smart remark from Dean.

"Oh...I'm sorry." Dean says with clear sympathy, "That's too bad."

"Yeah, well, y'know..." Castiel says, quite shocked at Dean's soft and caring response, "Yeah."

There's a slightly awkward pause before Castiel returns the questioning. After all, it's only polite, and Dean probably is having a better time than him, so it'll be good to hear some good news about someone's relationship.

"What about you?" He asks.

"I'm fine." Dean replies, smiling softly at him.

"How's married life?" Castiel asks, watching Dean dip his head as he fidgets with one of the books on the display table they're standing at.

"Not so good, I...uh..." Dean begins, "I'm getting a divorce."

"Oh, I'm sorry..." Castiel breathes, "Yeah, I'm really sorry."

"Yeah, well, what're you gonna do?" Dean sighs sadly, "What happened with you guys?"

* * *

><p>"When Nick and I started seeing each other, we wanted exactly the same things."<p>

Castiel and Dean are sat in a small restaurant with coffees, and Dean is listening intently as Castiel tells him what he knows will be quite a long story. He doesn't mind. It's nice to hear from Castiel again after all this time. Even better that it's in person.

"We wanted to live together but we weren't going to get a civil partnership or marry, because every time someone we knew got married, it ruined their relationship. They practically never had sex again." Castiel says, "It's true. It's one of the secrets no-one ever tells you. I would sit with my girlfriends who have kids...Well...my one girlfriend who has kids. Jo. And she'd complain about how she and Crowley never did it anymore. She never even complained about it, now that I think about it, she just said it matter-of-factly. She said they were up all night, that they were exhausted all the time, that the kids just took every sexual impulse they had out of them."

God, he makes family life sound so glum to Dean, who's always wanted a larger family. He knows that he would adopt if he married a guy, or got a partnership with a guy, because adoption agencies really don't care about the orientation of the people adopting.

"Nick and I used to talk about, it and we'd say that we were so lucky that we had this wonderful relationship where we could have sex on the kitchen floor and not worry about the kids walking in...y'know...we could fly off to Rome at a moment's notice." Castiel says, sounding incredibly sad, "Then, one day I was taking Jo's little girl for the afternoon, because I'd promised to take her to the circus. And we were in the cab playing _I Spy_. I spy a mailbox, I spy a lamppost..."

Dean nods in understanding, noticing the emotion building up inside Castiel as he tells the story.

"And she looked out of the window, and there was this man and this woman with two little kids, and the man had one of the kids on his shoulders," Castiel continues, "And she just said, 'I spy a family'. And I just started to cry. I just started crying. And I went home, and I said, 'The thing is, Nick, we never do fly off to Rome at a moment's notice."

"And the kitchen floor?" Dean asks.

"Not once." Castiel replies shaking his head, "It's this very cold, hard Mexican ceramic tile. Anyway, we talked about it for a really long time, and I told him what I wanted, which was what he didn't want, so I said, 'I guess it's over', and he left. And the truth is I feel really fine. I mean, I am over him, I really am over him. That was it for him, that was the most that he could give, and the more I think about it, the more I'm convinced that I did the right thing."

"You sound really healthy." Dean says, slightly in shock.

"Yeah..." Castiel replies, not really sounding as though he agrees.

The sun is setting as they walk along seventy-seventh street about a half hour later, both silent until Castiel brings up what he considers to be quite a positive point.

"At least I got the apartment."

"Everyone says that to me too." Dean replies, "But what's so hard about getting an apartment? You read the obituaries, you find out who died and you tip the doorman. They should put the two sections together, real estate and obituaries: 'Mr Klein died today, leaving a wife, two children, and a spacious three-bedroom apartment with a wood-burning fireplace."

Castiel laughs at this, a nice moment filling the atmosphere between them. It's nice to finally be able to have a good, happy moment together.

"When we first met, I really didn't like you that much." Dean says, ruining that completely.

"I didn't like _you_." Castiel tells him.

"Yeah, you did." Dean replies, "You were just so uptight then. You're much softer now."

Castiel stops and puts his hands on his hips for a moment.

"Y'know, I hate that kind of remark." He says, "It sounds like a compliment, but really it's an insult."

"Okay, you're still as hard as nails." Dean tells him, like it's meant to make him feel better.

"I just didn't want to sleep with you, but you had to write it off as a character flaw," Castiel says, "Instead of dealing with the fact that it might have something to do with you."

"What's the statute of limitations on apologies?" Dean asks.

"Ten years." Castiel replies with a smile.

"Ooh, I can just get in under the wire." Dean says, and the two smile, continuing their journey and realising that they are slowly, slowly becoming friends.

-TBC-

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><p><strong>Hope you enjoyed! <strong>

**Thanks for reading so far! **

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